The present invention relates to 1-[3-(methylthio) butyryl]-2,6,6-trimethyl-cyclohexene and the corresponding 1,3-cyclohexadiene analog having the generic structure: ##STR3## wherein the dashed line could be a single or a double carbon-carbon bond, produced by the process of reacting methyl mercaptan with "beta-damascenone" or "beta-damascone" according to the reaction: ##STR4## and novel compositions using such 1-[3-(methylthio)butyryl]-2,6,6-trimethyl-cyclohexene and/or the corresponding 1,3-cyclohexadiene analog to augment or enhance the flavor and/or aroma of consumable materials.
There has been considerable work performed relating to substances which can be used to impart (augment or enhance) flavors and fragrances to (or in) various consumable materials. These substances are used to diminish the use of natural materials, some of which may be in short supply and to provide more uniform properties in the finished product.
Sweet, black tea-like, tobacco-like, cocoa-like "damascenone-like", chocolate-like, dried fruit-like and rose petal-like aroma characteristics and sweet, black tea-like, cocoa-like, "damascenone-like", chocolate-like, tobacco-like, dried fruit-like and rose petal-like flavor characteristics are particularly desirable for many uses in the foodstuff, chewing gum, toothpaste and medicinal product flavor area. Sweet, honey-like, rich, slightly, fruity, dried fruit-like, hay tobacco-like, raspberry-like, blackcurrant-like, cedarwood-like, Virginia tobacco-like and woody notes are desirable in tobacco and tobacco flavor compositions especially where these notes appear both in the main stream and in the side stream on smoking as well as prior to smoking. Floral, natural rose oil-like and earthy aromas are especially desirable in several types of perfume compositions.
Sulfur containing cycloaliphatic ketones for use in augmenting or enhancing the organoleptic properties of foodstuffs and perfumes are well known in the prior art. U.S. Pat. No. 3,979,422 discloses compounds having the structures: ##STR5##
Alkylthio aliphatic ketones for use in augmenting or enhancing the organoleptic properties of foodstuffs are also well known in the prior art. U.S. Pat. No. 3,952,062 discloses such alkylthio aliphatic ketones, having the generic structure: ##STR6## wherein R.sup.1 represents hydrogen or together with R.sup.4 represents a C--C bond, R.sup.2 represents hydrogen or together with R.sup.6 represents a dimethylmethylene group, or, when R.sup.6 is isopropyl, together with R.sup.5 represents a C--C bond, R.sup.3 represents hydrogen or together with R.sup.6 represents a dimethylmethylene group, R.sup.4 represents hydrogen or together with R.sup.1 represents a C--C bond, R.sup.5 represents hydrogen or when R.sup.6 signifies isopropyl together with R.sup.2 represents a C--C bond, R.sup.6 represents isopropyl or together with R.sup.2 or with R.sup.3 represents a dimethylmethylene group, R.sup.7 represents methyl, X represents a C--C double bond taking the place of a C--C single bond, m = 0 to 2, provided that when R.sup.2, R.sup.3 and R.sup.5 represent hydrogen, R.sup.6 represents isopropyl, R.sup.4 together with R.sup.1 represents a C--C bond, m = 0.
The methylthio derivatives of the present invention are not, however, disclosed or referred to implicity or explicity in U.S. Pat. No. 3,952,062.
It is noteworthy that at column 3, of U.S. Pat. No. 3,952,062, the compounds having the structure: ##STR7## are indicated to be useful in foodstuff flavors and aroma where cabbage-like or onion-like aromas are desired. No such aromas are imparted or augmented or enhanced by the compounds of our invention.
Although the compounds of our invention having the generic structure: ##STR8## wherein the dashed line represents a carbon-carbon single bond or a carbon-carbon double bond have been determined to be existing in black tobacco oil, the compounds of our invention do not have organoleptic qualities which are even remotely similar to the organoleptic qualities of black tobacco oil.
Accordingly, the 1-[3-(methylthio)butyryl]-2,6,6-trimethyl-cyclohexene and/or the corresponding analog of our invention having the generic structure: ##STR9## wherein the dashed line represents a carbon-carbon double bond or a carbon-carbon single bond, have properties which are unexpected, unobvious and advantageous when compared to black tobacco oil where these compounds are found, and when compared to the compounds of the prior art, specifically those of U.S. Pat. Nos. 3,952,062 and 3,979,422.